Sodium Chloride → HCID 11960960, compound

HRID 1445315Notes

Reaction equation

HRID 1445315 reaction equation
[Na+].[Cl-].O=C[C@@H]([C@H]([C@@H]([C@@H](CO)O)O)O)O.[CH:15]([CH:17]([CH2:23][CH2:24][CH2:25][CH3:26])[C:18]([O:20][CH2:21][CH3:22])=[O:19])=[O:16].C1N=C(N)C2N=CN([C@@H]3O[C@H](COP(OP(OC[C@H]4O[C@@H](N5C=C(C(N)=O)CC=C5)[C@H](O)[C@@H]4O)(O)=O)(O)=O)[C@@H](O)[C@H]3O)C=2N=1.[OH-].[Na+]>S([O-])([O-])(=O)=O.[Zn+2].C(OCC)(=O)C>[OH:16][CH2:15][C@@H:17]([CH2:23][CH2:24][CH2:25][CH3:26])[C:18]([O:20][CH2:21][CH3:22])=[O:19]

Participants

8

Reactant 5

HCID 5234Sodium ChlorideHCID 14798Sodium HydroxideHCID 107526(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal2×HCID 439153NadhHCID 12592620Ethyl 2-formylhexanoate

Product 1

HCID 11960960HCID 11960960, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 24424Zinc SulfateCatalyst2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
30 °C

Procedure

Recombinant Escherichia coli HB101 (PNTRS) (Accession Number: FERM BP-08545) was inoculated in 50 ml of 2× YT medium (containing 1.6% of tripeptone, 1.0% of yeast extract, 0.5% of NaCl, and 50 mg of zinc sulfate.7H2O, pH=7.0) sterilized in a 500-ml Sakaguchi Flask and incubated while shaking at 30° C. for 40 hours. To 25 ml of the resultant culture solution, 1,000 units of glucose dehydrogenase (manufactured by Amano Enzyme Inc.), 2.5 g of ethyl 2-formylhexanoate, 3 mg of NAD, 4 g of glucose, and 50 mg of zinc sulfate.7H2O were added, the culture solution was stirred at 30° C. for 24 hours while adding 2.5 M aqueous solution of sodium hydroxide dropwise to the culture solution to adjust to pH 6.5. After completion of the reaction, 100 ml of ethyl acetate was added to the reaction solution for extraction and the organic layer was distilled off under reduced pressure. Thereafter, the product was purified by silica gel chromatography to obtain an oily ethyl (R)-2-hydroxymethylhexanoate. The yield was 90% and the optical purity was 93.6% e.e. Note that analysis for optical purity was performed as follows. The product was derivatized with a HPLC labeling agent (3,5-dinitrobenzoyl chloride), and analyzed by HPLC using a Chiralcel OD-H column, 0.46×25 cm I.D. (manufactured by Daicel Chemical Industries, Ltd.).

Workup

  1. addition7H2O were added
  2. stirringthe culture solution was stirred at 30° C. for 24 hours
  3. additionwas added to the reaction solution for extraction
  4. distillationthe organic layer was distilled off under reduced pressure
  5. customThereafter, the product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-27b990c8fbf94c66925523dcb9e09386
Source dataset
uspto-grants-2010_02
Patent number
US07666659B2

Reaction notes

Loading…